Synthesis of 2,5,6-trisubstituted benzimidazoles by heck and subsequent 6π-electrocyclization-dehydrogenation reactions of 2,4,5-tribromo-n- methylimidazole and 2-Aryl-4,5-dibromo-N-methylimidazoles

Synlett

Volumn , Issue 12, 2010, Pages 1779-1782

  Toguem, Serge Mithérand Tengho ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

benzimidazole; catalysis; electrocyclization; Heck reaction; palladium

Indexed keywords

2 ARYL 4,5 DIBROMO N METHYLIMIDAZOLE DERIVATIVE; 2,4,5 TRIBROMO N METHYLIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DEHYDROGENATION; DRUG SYNTHESIS; HEATING; HECK REACTION; PROCESS OPTIMIZATION; STRUCTURE ANALYSIS;

EID: 77954835789     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258092     Document Type: Article

References (39)

1. Römpp Lexikon Naturstoffe Steglich W Fugmann B Lang-Fugmann S Thieme Stuttgart 1997
2. Alamgir M, Black D S. C., Kumar N, Top. Heterocycl. Chem. Springer Berlin 2007 87-118
3. Imidazole and Benzimidazole Synthesis Grimmett M R. Academic Press Boston 1997
4. Spasov A A., Yozhitsa I N., Bugaeva L I., Anisimova V A., Pharm. Chem. J. 1999 33 6
5. Benzimidazoles and Cogeneric Tricyclic Compounds, In The Chemistry of Heterocyclic Compounds Part 1, Vol. 40 Preston P N. Wiley-VCH Weinheim 1981
6. Grimmett M R., Imidazoles, In Comprehensive Heterocyclic Chemistry II Vol. 3 Katritzky A R. Rees C W. Scriven E F. V. Elsevier Amsterdam 1996 77-220
7. Grimmett M R., Imidazole and Benzimidazole Synthesis Academic Press Boston 1997
8. Brown E G., Ring Nitrogen and Key Biomolecules Kluwer Academic Press Boston 1998
9. Gilchrist T L., Heterocyclic Chemistry The Bath Press Bath 1985
10. Kucukbay H, Durmaz R, Guven M, Gunal S, Arzneim.-Forsch. 2001 51 420
11. Kawato H C., Nakayama K, Inagaki H, Ohta T, Org. Lett. 2001 3 3451
12. Weidner-Wells M A., Ohemeng K A., Nguyen V N., Fraga-Spano S, Macielag M J., Werblood H M., Foleno B D., Webb G C., Barrett J F., Hlasta D J., Bioorg. Med. Chem. Lett. 2001 11 1545
13. Kennedy G, Viziano M, Winders J A., Cavallini P, Gevi M, Micheli F, Rodegher P, Seneci P, Zumerle A, Bioorg. Med. Chem. Lett. 2000 10 1751
14. Navarrete-Vazquez G, Cedillo R, Hernandez-Campos A, Yepez L, Hernandez-Luis F, Valdez J, Morales R, Cortes R, Hernandez M, Castillo R, Bioorg. Med. Chem. Lett. 2001 11 187
15. Lopez-Rodriguez M L., Benhamu B, Viso A, Murcia M, Pardo L, Tetrahedron 2001 57 6745
16. Lopez-Rodriguez M L., Benhamu B, Ayala D, Rominguera [nl]J L., Murcia M, Ramos J A., Viso A, Tetrahedron 2000 56 3245
17. Chackalamannil S, Doller D, Eagen K, Czamiecki M, Ahn H S., Foster C J., Boykow G, Bioorg. Med. Chem. Lett. 2001 11 2851
18. For reviews of cross-coupling reactions of polyhalogenated heterocycles, see:, Schröter S, Stock C, Bach T, Tetrahedron 2005 61 2245
19. Schnürch M, Flasik R, Khan A F., Spina M, Mihovilovic M D., Stanetty P, Eur. J. Org. Chem. 2006 3283
20. Dang T T., Dang T T., Ahmad R, Reinke H, Langer P, Tetrahedron Lett. 2008 49 1698
21. Dang T T., Villinger A, Langer P, Adv. Synth. Catal. 2008 350 2109
22. Hussain M, Nguyen T H., Langer P, Tetrahedron Lett. 2009 50 3929
23. TenghoToguem S.-M, Hussain M, Malik I, Villinger A, Langer P, Tetrahedron Lett. 2009 50 4962
24. Hussain M, Malik I, Langer P, Synlett 2009 2691
25. Hussain M, Zinad D S., Salman G A., Sharif M, Villinger A, Langer P, Synlett 2010 276
26. Dang [nl]T T., Dang T T., Rasool N, Villinger A, Langer P, Adv. Synth. Catal. 2009 351 1595
27. Kawasaki I, Yamashita M, Ohta S, Chem. Pharm. Bull. 1996 44 1831
28. Kawasaki I, Yamashita M, Ohta S, J. Chem. Soc., Chem. Commun. 1994 2085
29. Revesz L, Bonne F, Makavou P, Tetrahedron Lett. 1998 39 5171
30. Revesz L, Di Padova F E., Buhl T, Feifel R, Gram H, Hiestand P, Manning U, Wolf R, Zimmerlin A G., Bioorg. Med. Chem. Lett. 2002 12 2109
31. Kawasaki I, Katsuma H, Nakayama Y, Yamashita M, Ohta S, Heterocycles 1998 48 1887
32. Wang D, Haseltine J, J. Heterocycl. Chem. 1994 31 1637
33. For previous syntheses of benzimidazoles containing ester groups located at carbon atoms C-5 and C-6, see:, Cummings C G., Ross N T., Katt W P., Hamilton [nl]A D., Org. Lett. 2009 11 25
34. Kalindjian S B., Dunstone D J., Low C M. R., Pether M J., Roberts S P., Tozer M J., Watt G F., Shankley N P., J. Med. Chem. 2001 44 1125
35. Neochoritis C, Livadiotou D, Stephanidou-Stephanatou J, Tsoleridis C A., Tetrahedron Lett. 2007 48 2275
36. For reviews of domino reactions, see:, Tietze L F., Beifuss U, Angew. Chem., Int. Ed. Engl. 1993 32 131
37. Angew. Chem. 1993, 105, 137
38. Tietze L F., Chem. Rev. 1996 96 115
39. De Meijere and coworkers reported twofold Heck reactions of 1,2-dibromocycloalk-1-enes and related substrates and subsequent 6-electrocyclization:, Voigt K, von Zezschwitz P, Rosauer K, Lansky A, Adams A, Reiser O, de Meijere A, Eur. J. Org. Chem. 1998 1521; and references cited therein. For examples from our group, see ref. 8c-e